Tetrahydrofuran → 3-(3-(4-Phenylamino-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

HRID 1891697노트

반응식

HRID 1891697 반응식
O1CCCC1.[C:6]1([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[N:21][OH:22])=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:24]([C:26]1[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=1)#[CH:25].C(N(CC)CC)C>O>[C:6]1([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]4[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=4)[O:22][N:21]=3)=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 72262877(4-Phenylamino-phenyl)-acetohydroximoyl chloride

생성물 1

HCID 592552833-(3-(4-Phenylamino-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine수율 38.2%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

To a tetrahydrofuran (3 mL) solution of (4-phenylamino-phenyl)-acetohydroximoyl chloride (150 mg, 0.576 mmol) described in Manufacturing Example 69-1-4 and 3-ethynyl-pyridin-2-ylamine (43 mg, 0.367 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (201 μL, 1.44 mmol) at room temperature, which was stirred for 7 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (48 mg, 24%).

후처리

  1. extractionwhich was then extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1)

출처 및 근거

ORD 기록
ord-44e1be6aa2104997b2f8ab7d26d98ed1
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507530B2

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